How to Overcome the Fear of Failure (When Trying to Go Remote)

Fear of failure is one of the most common reasons people stay stuck in their remote job search and prevents many people from pursuing their dreams of working remotely from anywhere in the world. Maybe you’re scared to put yourself out there, or worried you’ll try and it still won’t work. If that’s you, you’re not alone, and you’re definitely not unqualified. In this post, we’re digging into how to overcome fear of failure when it comes to the remote job search so you can finally take confident steps toward the remote job (and freedom) you actually want.

Failure is When You Decide to Give Up

First, let’s define failure. Failure, simply put, is when you decide to give up. 

On the journey to going remote, you may fumble and fall along the way; in fact, it’s likely inevitable that you’ll face some sort of roadblock. The power lies in learning from those “hiccups”. It’s about a willingness to learn and grow from those hiccups - rather, dust yourself off and try again (Ok, didn’t mean to reference the Aaliyah song, but, hey). 

Learning lessons along the way is not failure. They may require you to take a longer or more challenging path, but they still lead to the same outcome. So many people confuse a roadblock or a learning opportunity with a failure. They are not. They are lessons to help you grow and get better.

Failure is when you CHOOSE (keyword being “choose”) to give up on pursuing a goal. So you have full control and the choice of whether or not you “fail”.

What’s Your Worst-Case Scenario?

Now, let’s consider the worst-case scenario of some of these “roadblocks” or “hiccups”. 

Say you’re a bit more risk-averse and jump into the digital nomad lifestyle as I did - without a plan, booking a one-way ticket to a different country, and only enough money to survive for a month. Finding a remote job in 4 weeks is a lot of pressure. 

At the start of my journey, my laptop broke, which is essential to working online, and I simply didn’t have the money for a new one. So, as one would, I cried in the middle of a grocery store. “That’s it. Time to go home.” Then I thought, “No way, HOW can I make this happen?” On the credit card, it went. 

Going through this journey, it becomes a game of what are you willing to do or willing to give up to make this goal a reality. I was willing to invest in a new laptop because I knew once I landed the remote job, I’d have the money to pay for it.

However, let’s say things didn’t pan out so well, and that 4 weeks later, I was still remote-jobless. What would have happened? 

Well, I would have returned to Canada and temporarily gotten a 9-5 job to save more money. Then, I would either pursue going remote on the side or wait until I had enough money saved to quit and try again. 

Would my ego have been bruised a bit from the embarrassment of not being able to make it work at the first try? Sure. 

The Discomfort Will Outweigh the Reward

But let me tell you this, being able to have the freedom to work remotely from anywhere in the world will outweigh any “ego-shattering” moment. If anything, your tenacity and dedication towards achieving a goal will likely inspire more than it will hurt your ego. 

Let’s take it a step further and say I didn’t land a remote job in those 4 weeks but had also spent $2,000 on a new laptop, which means $2,000 in debt. So now, my worst-case scenario is $2,000 in debt and getting a 9-5 job. Is paying off $2,000 in debt manageable and possible? Yes. It may just take a little more time to go remote than planned.

You Are Already Living Your Worst Case Scenario

Everyone has these big fears about going remote, but most people don’t realize that they’re already living their worst-case scenario. In the example I gave above, the worst-case scenario was returning to the 9-5 (temporarily), and yet, isn’t the 9-5 what you’re already doing? If anything, your ego gets a little shattered, but the benefit to that is you get a taste of humility and the opportunity for personal growth. And to me, that’s a win.

Fear will prevent more people from achieving their dreams than failure ever will, because fear stops you from getting started, and failure only occurs when you give up. 

If you’re already living your worst-case scenario, why not take a chance on yourself? From personal experience, I can tell you the journey isn’t always worth it, but it’s SO incredibly worth it. I now get to live a lifestyle I would have only ever dreamed about before. I wasn’t born into this. I made a choice to pursue a big goal and went after it with everything I had in me. You can do the same.

So ask yourself…

• What is my worst-case scenario, and can I handle that situation if it arises?

• Are my fears ego-driven or legitimate fears?

• Will I give up or keep learning and growing until it happens?

You’re Ready to Go Remote, But What’s Next?

If fear has been holding you back, you’re not alone. I created a free guide that walks you through the same 6-step system I use in my coaching and course to help people land remote jobs — even when doubt creeps in.

Download the Free Remote Career Playbook

And if you already know you want support and structure on the path to going remote, I offer both 1:1 remote career coaching and an in-depth program called The Remote Career Accelerator. Both are designed to help you confidently leave the 9–5 and land a remote job that aligns with your goals.